Stereochemistry of benzodihydrofuran-2-carboxylic acid ester photorearrangement

…, JJ Napier, P Sundararaman

Index: Schultz,A.G.; Napier,J.J.; Sundararam,P. Journal of the American Chemical Society, 1984 , vol. 106, p. 3590

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Citation Number: 4

Abstract

Abstract: The stereoselectivity of the photorearrangement of benzodihydrofuran la to give phenol 3 is determined by preparation and irradiation of optically active la. Chiral shift reagent NMR analysis of recovered la and derivatized 3 (in the form of spirocyclic selenide 22) indicates that configuration is not lost during the irradiation. A mechanism involving concerted photorearrangement of la to spiro [cyclopropane-2', 4'-cyclohexadien-1'-one] 2 ...